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Phytochemical Constituents and Pharmacological Activities of Plants from the Genus Adiantum : a Review

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Phytochemical Constituents and Pharmacological Activities of Plants from the Genus Adiantum : a Review Pan et al Tropical Journal of Pharmaceutical Research October 2011; 10 (5): 681-692 © Pharmacotherapy Group, Faculty of Pharmacy, University of Benin, Benin City, 300001 Nigeria. All rights reserved . Available online at http://www.tjpr.org http://dx.doi.org/10.4314/tjpr.v10i5.18 Review Article Phytochemical Constituents and Pharmacological Activities of Plants from the Genus Adiantum : A Review 1 1 1 1 1 2 C Pan , YG Chen *, XY Ma , JH Jiang , F He and Y Zhang 1Department of Chemistry, Yunnan Normal University, Kunming 650500, 2School of Pharmacy, Kunming Medical College, Kunming 650031, China. Abstract Adiantum is a genus of ca. 200 species in the family Adiantaceae, distributed extensively across the world from cool temperate zones to hot tropical regions. A lot of Adiantum species have been used in traditional Chinese medicine to cure human and animal diseases including relief of internal heat or fever, enhancement of urination, removal of urinary calculus, and sundry other curative claims. Chemical studies have shown the presence of various classes of compounds, the main ones being triterpenoids, flavonoids, phenyl propanoids, steroids, alicyclic acids, lipids and long-chain compounds. The extract of this genus as well as pure compounds isolated from it have been demonstrated to possess multiple pharmacological activities such as analgesic, antinociceptive, anti-implantation, and antimicrobial activities. In this review, we have addressed the phytochemistry and pharmacological activities of the Adiantum species in order to collate existing information on this plant as well as highlight its multi-activity properties as a medicinal agent. Keywords: Adiantum species, Adiantaceae, Phytochemical constituents, Pharmacological activities. Received: 10 February 2011 Revised accepted: 13 September 2011 *Corresponding author: E-mail: [email protected]; +86 871 5941089 Trop J Pharm Res, October 2011;10(5): 681 Pan et al INTRODUCTION neohopene, fernane, isofernene, filicane, pteronane and adiane types. The presence of Adiantum is a genus of ca . 200 species in the a large number of the nor-compounds is also family Adiantaceae, distributed extensively a characteristic feature of this genus. over the world from cool temperate zones to Hopane-type triterpenoids, 1-9, were isolated hot tropical regions. As many as 30 species from various Adiantum species, such as A. and 5 varieties are found in China [1]. Half of capillus-veneri, A. edgeworthii, A. the species have been used in traditional monochlamys, A. caudatum, A. incisum, A. Chinese medicine to cure human and animal cuneatum, A. pedatum, A. tetraphyllum and diseases including relief of internal heat or A. lunulactum (syn. A. philippense ) (Table 1, fever, enhancement of urination, removal of Figure 1) [3,15-26]. Isohopane-type urinary calculus, elimination of stasis to triterpenoid, 10 , was isolated from A. resolve swelling, relief of cough, cure of lunulatum [27], and neohopane-type diarrhea and stoppage of bleeding, as well as triterpenoids, 11 -16 were also isolated from treatment of urinary tract infection, calculus, the genus Adiantum (Table 2, Figure 2). hepatitis, hemorrhage, fractures, snakebite, burns and scald [2]. Other migrated hopane or closely related triterpenoids isolated from the genus According to the literature, Adiantum species Adiantum include norhopane-type are a rich source of triterpenes with various triterpenoids, 17 -29 (Table 3, Figure 3), structural skeletons. Besides, flavonoids, fernane-type triterpenoids, 30 -51 (Table 4, phenyl propanoids and sterols have been Figure 4), an isofernane-type triterpenoid, isolated from the genus Adiantum [3-14]. isofernene ( 52 ) isolated from A. These compounds have been reported to monochlamys and A. pedatum [19,40] , show various bioactivities, such as analgesic, adiane-type triterpenoids, 53 -57 , and filicane- antinociceptive, anti-implantation, and type triterpenoids, 58 -67 (Table 5, Figure 5), antimicrobial activities. In this review, we and a pteronane-type triterpenoid, pteron-14- summarize the current knowledge of the en-7α-ol obtained from A.capillus-veneris phytochemistry of the plants as well as the [16]. Secofilicanes 66 and 67 isolated from A. compounds that have been isolated from the cuneatum are the first two secotriterpenoids genus Adiantum . The biological activities of that have been reported in ferns. Adipedatol this genus have also been addressed. (28 ) and filicenal (61 ) are the first two examples of the natural triterpenoids having PHYTOCHEMISTRY the hemiketal and the conjugated aldehyde groups, respectively [23,28,35,40]. Since the 1960s, 124 compounds, including terpenoids, flavonoids, phenyl propanoids, Other pentacyclics include lupane and steroids, alicyclic acids, lipids and long-chain norlupane triterpenoids lup-20(29)-en-28-ol, compounds have been reportedly isolated 24-norlupan-3-one and adiantulupanone from the genus. Triterpenoids and flavonoids isolated from A. capillus-veneris, A. are the dominant constituents within the tetraphyllum and A. venustum [3,47,48]. genus Adiantum . Oleanane triterpenoids olean-12-en-3-one and olean-18-en-3-one were isolated from A. Terpenoids capillus-veneris [15,25]. Noroleanane triterpenoids adininaonol and Eighty-five triterpenoids were isolated from adiantuoleanone were isolated from A. the genus Adiantum [3-5,15-52]. Most of the venustum and A. incisum respectively triterpenoids are pentacyclic and belong to [21,48]. Ursane triterpenoid urs-20-en-16-ol the hopane and migrated hopane or closely was isolated from A. capillus-veneris [47] , related groups such as isohopane, and gammacerane triterpenoids tetrahyma- Trop J Pharm Res, October 2011;10(5): 682 Pan et al Table 1: Hopane-type triterpenoids from the genus Adiantum No. Compound name Source* Ref. 1 Hop-22(29)-ene (= Diploptene) A1~A3 15-19 2 17 β,21 β-Epoxyhopane A4 20 3 Adininaneone A5 21 4 Hydroxyhopane (= Hopanol) A1,A2,A6~A8 3,15-17, 22,23 5 Mollugogenol A A9 24 6 6α-Acetoxy-16 β,22-dihydroxy-3-ketoisohopane A1,A9 24,25 7 17,29-Epoxyhopane A1 16 8 Hopan-28,22-olide A1 16 9 3β-Acetoxy-6α-hydroxy-hop-15,17(21)-diene A9 26 * A1=A. capillus-veneris, A2=A. edgeworthii, A3=A. monochlamys, A4=A. caudatum, A5= A. incisum, A6= A. cuneatum, A7=A. pedatum, A8= A. tetraphyllum, A9= A. lunulatum O O O 1 2 8 Figure 1: Selected hopane-type triterpenoids from the Genus Adiantum Table 2: Isohopane and neohopane-type triterpenoids from the Genus Adiantum No. Compound name Source* Ref. 10 3β-Acetoxy-21 αH-hop-22(29)-ene A9 27 11 Neohop-12-ene (= Neohopene) A1~A3,A6,A7 15-18, 23, 28,29 12 Neohop-18-en-12 α-ol A6 30 13 13-Epineohop-18-en-12 α-ol A6 30 14 Neohop-13(18)-ene A3,A4,A7 18, 20, 23,29 15 Neohop-13(18)-en-19 α-ol A6 30 16 Neohopa-11,13(18)-diene A3,A6,A7 18, 23, 28,29 * A1=A. capillus-veneris, A2=A. edgeworthii, A3=A. monochlamys, A4=A. caudatum, A6= A. cuneatum, A7=A. pedatum, A9= A. lunulatum R AcO R 14 H 10 11 15 OH Fig 2 : Selected isohopane and neohopane-type triterpenoids from the Genus Adiantum Trop J Pharm Res, October 2011;10(5): 683 Pan et al Table 3: Norhopane-type triterpenoids from the genus Adiantum No. Compound name Source* Ref. 17 Trisnorhopane A1,A6 16,28 18 Isoglaucanone A1,A6,A7 15, 16, 23,28 (= 17 αH-Trisnorhopan-21-one) 19 Glaucanol A A7 23 20 Glaucanol B acetate A6 28 21 21-Hydroxy-30-norhopan-22-one A1,A3,A6,A7,A10,A11 15, 16, 18, 23, 28,31-33 (= 21-Hydroxyadiantone, Hydroxyadiantone) 22 Isoadiantone A1,A3~A7,A12 15,16,18,20,21, 23,28,33-38 23 Adiantone A1~A7,A9,A10,A13 4,5,15-18, 20, 21,23, 28, 31, 36,37,39-41 24 19 α-Hydroxyadiantone A2,A4 17,20 25 29-Norhopan-22-ol A4 4 26 Isoadiantol B [= (22S)-30- A1,A3,A6,A7,A11 15,18, 22, 23,32 Norisohopan-22-ol, Isoadiantol] 27 22,29 ξ-Epoxy-30-norhopane-13 β-ol A9 39 28 Adipedatol A7 23,40 29 Adipedatol Me ether A7 40 * A1= A. capillus-veneris, A2= A. edgeworthii, A3= A. monochlamys, A4 =A. caudatum, A5= A. incisum, A6= A. cuneatum, A7= A. pedatum, A9= A. lunulatum, A10= A. venustum, A11= A. Emarginatum nol, epihakonanediol, ketohakonanol (= from A. tetraphyllum [3] while hyperin and oxohakonanol) and hakonanediol were trifolin have been isolated from A. isolated from A. monochlamys [18]. monochlamys and A. malesianum Tetrahymanol and ketohakonanol were also respectively [6,9]. Quercetin 3-O-(6"- isolated from A. capillus-veneris , A. pedatum , malonyl)-D-galactoside, rutin, isoquercetin, A. emarginatum , A. cuneatum and A. incisum querciturone, kaempferol 3-glucuronide, [22,23,32,33,49]. astragalin, keampferol 3-sulphate, kaempferol 3,7-diglucoside, nicotiflorin and Besides, tetracyclic triterpenoids have been kaempferol 3-O-rutinoside sulfate were isolated from A. venustum , including isolated from A. capillus-veneris lanostane triterpenoids adiantulanosterol, [7,8,10,12,13]. Querciturone and kaempferol lanost-20(22)-en-3,19-ether and adiantulano- 3-glucuronide were also isolated from A. stene, as well as tirucallane triterpenes cuneatum [7]. Isoquercetin has also isolated adiantutirucallenes A and B [48, 50-52]. from A. monochlamys, A. caudatum, A. tetraphyllum, A. venustum and A. Diterpenoids, 8,13-epoxy-14-labden-19-oic aethiopicum [3-6] while astragalin was acid has been isolated from A. emarginatum isolated from A. monochlamys, A. cuneatum, [32], and linear diterpenoids phytol and A. venustum and A. aethiopicum [5, 6,11]. phyten-3(20)-1,2-diol were isolated from A. tetraphyllum [3] . Only one tetraterpenoid, α- Flavanone prunin was obtained from A. carotene monoepoxide was isolated from A. monochlamys and A. aethiopicum venustum [5] . respectively [6]. Flavandiol, leucopelargonidin was isolated from A. venustum [5]. 2',4',6'- Flavonoids Trihydroxychalcone were isolated from A. sulphureum [14]. Flavone C-glucosides Flavonoids (18 of them) have been isolated vitexin and isovitexin were isolated from A.
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